Phenol → 2-Allylphenol

Temperature

100 °C

To a reaction bottle was added 8.0 moles of phenol (753 grams) dissolved in 1,200ml of isopropanol. To this was added 8.0 moles of sodium hydroxide (320 grams) dissolved in 300ml of water. The bottle was rinsed three times by adding each time 200ml of isopropanol with reaction of the sodium hydroxide and phenol occurring immediately. Allyl chloride, in an amount of 9.6 moles, was charged. The mixture was then agitated and heated. A slight nitrogen pressure of approximately 70 kPa (10 psig) was placed on the reaction bottle. The reactor was brought up to a temperature of approximately 70° C. After approximately 5 hours at 70° C, the formation of allyl phenyl ether was judged complete and the reaction bottle was allowed to come to room temperature. The reaction mixture was then washed twice with 3 liters of water to remove sodium chloride, isopropanol, and unreacted sodium phenoxide as well as other by-products. The bottle was then charged with 3 liters of toluene, mixed, and heated to a temperature of approximately 100° C. An azeotropic distillation occured and was continued for approximately 3 hours during which time the toluene was distilled off along with traces of water, isopropanol, unreacted allyl chloride, and other by-products. The remaining allyl phenyl ether was sufficiently pure to be thermally rearranged to 2-allyl phenol. The rearrangement process occurred at 200° C and continued for approximately 5 hours. After this time, the reaction was stopped and a gas chromatographic analysis of the product was made. A 2-allyl phenol yield of 90.6 percent was achieved.

1. washThe bottle was rinsed three times
2. additionby adding each time 200ml of isopropanol
3. customwith reaction of the sodium hydroxide and phenol occurring immediately
4. temperatureheated
5. customwas brought up to a temperature of approximately 70° C
6. customto come to room temperature
7. washThe reaction mixture was then washed twice with 3 liters of water
8. customto remove sodium chloride, isopropanol, and unreacted sodium phenoxide as well as other by-products
9. additionThe bottle was then charged with 3 liters of toluene
10. additionmixed
11. distillationAn azeotropic distillation
12. waitwas continued for approximately 3 hours during which time
13. distillationthe toluene was distilled off along with traces of water, isopropanol, unreacted allyl chloride, and other by-products
14. customoccurred at 200° C
15. waitcontinued for approximately 5 hours

ORD record

ord-02e4ec2cae704f4fb0b65d943efb15f6

Source dataset

uspto-grants-1977_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04060563